Stabilized DCD and/or alkyl thiophosphoric triamide solvent systems and use in agricultural applications

ABSTRACT

An inhibitor composition contains alkyl thiophosphoric triamide (or a mixture of alkyl thiophosphoric triamide and dicyandiamide), dissolved in a liquid medium comprising at least one organic solvent, at least one amine stabilizer and, optionally, at least one dye and/or at least one odor masking agent, is useful in making fertilizer compositions and in a method of fertilizing target plants.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a continuation of U.S. patent application Ser. No.16/415,024 filed May 17, 2019 which is a continuation of U.S. patentapplication Ser. No. 15/637,110 filed Jun. 29, 2017 (now patented asU.S. Pat. No. 10,336,660) which claims the benefit of U.S. ProvisionalApplication Ser. No. 62,356,035, filed Jun. 29, 2016, incorporatedherein by reference in its entirety.

FIELD OF THE INVENTION

This invention relates to stabilized liquid compositions comprisingdicyandiamide and/or an alkyl thiophosphoric triamide, methods forstabilizing such liquid compositions and the use of such compositions.

BACKGROUND OF THE INVENTION

In the agrochemical industry, farmers use various fertilizers to impartmacronutrients to plants either by application to the soil orapplication to plant leaves. Nitrogen, phosphorus, potassium, calcium,magnesium, and sulfur are macronutrients that must be supplied to theplants and soil manually by farmers. In many crops, the amount ofnitrogen supplied is critical to the overall quality and growth of thecrop. Nitrogen is typically supplied in the form of nitrogenous, i.e.,nitrogen precursor-containing, fertilizer compounds, such as urea,ammonium nitrate, or ammonium phosphate fertilizer compounds. Due to thehigh water solubility of these salts, however, applied nitrogen valuesmay be lost due to run-off and leaching of the nitrogenous fertilizercompounds. Once applied, the nitrogenous fertilizer compounds aretypically degraded, for example, by microorganisms present in the soil,to nitrogenous species such as NH₄ ⁺, NO₂ ⁻, NO₃ ⁻, and ammonia gas,that may be even more readily lost through evaporation, run-off, andleaching than the fertilizer compounds themselves. If degradation of thefertilizer compounds occurs at a rate that is faster than thenitrogenous degradation products can be used by the plants, then thenitrogen values in the degradation products are at increased risk ofbeing lost.

Nitrification and/or urease inhibitors are of potential use in delayingdegradation of fertilizer compounds and thereby reducing losses ofnitrogenous degradation products that would otherwise occurred in theabsence of the inhibitors. The use of nitrification and/or ureaseinhibitors in combination with nitrogenous fertilizer compounds tends toincrease the amount of time the nitrogen sources remain in the soil andavailable for absorption by the plants, which tends to increase theeffectiveness of the fertilizers and positively impact crop yield andquality.

Aqueous end use fertilizer solutions are typically prepared in the fieldby diluting commercially available concentrated fertilizer compositionswith water. Commonly used concentrated fertilizer compositions includeconcentrated ammonium nitrate compositions, such as, for example, UAN18, UAN 28, UAN 30 and UAN 32.

Dicyandiamide is potentially useful as a nitrification inhibitor in suchaqueous end use fertilizer compositions, but has very low solubility(about 41 grams per liter (“g/l”) in water and so is difficult to beincorporated into the aqueous end use fertilizer compositions,particularly under field conditions.

SUMMARY OF THE INVENTION

Urease inhibitors can be used with a fertilizer (i.e., incorporated intoa urea-containing fertilizer, e.g., urea and urea ammonium nitrate(UAN)) to slow the conversion of ammonium to ammonia gas and thus slowthe loss of ammonia to volatilization, thus making ammonium available toplants in the soil for longer periods of time. In many crops, the amountof nitrogen supplied is critical to the overall quality and growth ofthe crop. Nitrogen is supplied in either urea or ammonium phosphateforms. Due to the high water solubility of these salts, however, much ofthe nitrogen applied is lost to run-off and leaching. In ammonium-basedproducts, if the nitrogen is not lost due to leaching or run-off, it isbeing converted to ammonia gas by an enzyme called urease where theammonium ions can bind to soil particles. Conversion occurring near thesurface of the soil, however, does not allow for binding and thisammonia is lost to the atmosphere. Urease inhibitors are used to protecta farmer's investment in fertilizers by preventing the breakdown of ureaby urease, the soil microbe responsible for converting urea to usableammonia in the soil. This increases the amount of time the nitrogenremains in the soil and is available to the plant for absorption.

Similarly, nitrification inhibitors can be used with a fertilizer (i.e.,incorporated into a urea-containing fertilizer, e.g., urea and ureaammonium nitrate (UAN)) to slow the process of ammonium conversion tonitrate, and subsequently the loss of nitrate to leeching, thus makingammonium available to plants in the soil for longer periods of time.Ammonium is one of the main forms of nitrogen that can be utilized byplants. Increasing the amount of time that the nitrogen is available tothe plant increases the effectiveness of the fertilizer which positivelyimpacts crop yield and quality.

Fertilizers, in one embodiment, are common water soluble inorganicfertilizers that provide nutrients such as phosphorus-based,nitrogen-based, potassium-based or sulphur-based fertilizers. Examplesof such fertilizers include: for nitrogen as the nutrient: nitrates andor ammonium salts such as ammonium nitrate, including in combinationwith urea e.g. as Uram type materials, calcium ammonium nitrate,ammonium sulphate nitrate, ammonium phosphates, particularlymono-ammonium phosphate, di-ammonium phosphate and ammoniumpolyphosphate, ammonium sulphate, and the less commonly used calciumnitrate, sodium nitrate, potassium nitrate and ammonium chloride. It isunderstood that a fertilizer composition can comprise one or acombination of the fertilizers described herein.

A typical urease inhibitor, alkyl thiophosphoric triamide (for example,N-(n-butyl)-thiophosphoric triamide or otherwise “NBPT”), however, facesdrawbacks in its use as NBPT is extremely difficult to handle. NBPT is asticky, waxy, heat and water sensitive material, which cannot be used inits solid form, as it is used at low concentrations making it difficultto evenly distribute on urea prills (i.e., large granules) and in soil.In order to evenly distribute the NBPT onto the urea, the NBPT should bedispersed into a carrier prior to being sprayed onto the urea. Thus, theuse of a solvent system containing the NBPT is desirable as, in itsliquid form, the solvent system is capable of distributing the NBPT intogranular urea (e.g., urea prills) and into liquid fertilizers containingurea. By introducing the NBPT to liquid fertilizers containing urea (forexample, urea-ammonium nitrate solutions or UAN) in a solvent system,the NBPT is capable of being better dispersed in the liquid fertilizer.

Dicyandiamide is useful as a nitrification inhibitor in aqueousagricultural applications, e.g., end use fertilizer compositions, butsimilar to urease inhibitors face drawbacks. Nitrification inhibitors,such as dicyandiamide, generally have very low solubility (about 41grams per liter (“g/l”) in water and so it is difficult to incorporateinto the aqueous end use fertilizer compositions, particularly underfield conditions. As nitrification inhibitors, such as dicyandiamide,have a generally low solubility, they are used at low concentrations inwater making it difficult to evenly distribute on urea-containing prills(i.e., large granules) and in soil. In order to evenly distribute thedicyandiamide onto the urea-containing prills or granules, dicyandiamideshould be dispersed into a solvent carrier prior to being sprayed ontothe urea. Thus, the use of a solvent system containing dicyandiamide(herein, also termed “DCD”) is desirable as, in its liquid form, thesolvent system is capable of distributing the dicyandiamide onto ureagranules or prills, urea ammonium nitrate granules or prills or,otherwise, urea-containing granules or prills, and into liquidfertilizers containing urea or urea ammonium nitrate. By introducing thedicyandiamide to liquid fertilizers containing urea (for example,urea-ammonium nitrate solutions or UAN) in a solvent system, thedicyandiamide is capable of being better dispersed in the liquidfertilizer.

In one embodiment, concentrated fertilizer compositions includeconcentrated ammonium nitrate compositions, such as, for example, UAN18, UAN 28, UAN 30 and UAN 32.

Thus, in one embodiment, it is desirable to have a solvent systemcontaining alkyl thiophosphoric triamide, for example,(N-(n-butyl)-thiophosphoric triamide), that has a favorabletoxicological and/or ecological profile and desirable characteristics interms of low volatility, biodegradability or ready biodegradability(i.e., readily biodegradable), low toxicity or low hazard level. Inanother embodiment, it is desirable to have a solvent system containinga nitrification inhibitor, for example, dicyandiamide, that has afavorable toxicological and/or ecological profile and desirablecharacteristics in terms of low volatility, biodegradability or readybiodegradability (i.e., readily biodegradable), low toxicity or lowhazard level. In a further embodiment, it is desirable to have a solventsystem containing a combination of a nitrification inhibitor and ureaseinhibitor that has a favorable toxicological and/or ecological profileand desirable characteristics in terms of low volatility,biodegradability or ready biodegradability (i.e., readilybiodegradable), low toxicity or low hazard level.

Another problem is that certain nitrification inhibitors and/or ureaseinhibitors degrade at varying temperatures and extreme conditions, e.g.,high temperatures or low temperatures. For example, NBPT—a ureaseinhibitor—degrades rapidly at higher temperature, typically, above 45°C. Often times temperatures in agricultural fields (e.g., corn fields,wheat fields, etc.) reach in excess of 35° C. and sometimes can reach upto 45° C. or higher. For example, at 45° C. NBPT formulated in differentsolvents changes color in days from colorless to a darker green/brown,followed by sludge/precipitate formation after weeks had been exposed tohigh heat. Thus, it is also desirable to have solvent systems containingnitrification inhibitors and/or urease inhibitors that are stable athigh temperatures, such as those utilized in hot climates or weather.This invention addresses the addition of stabilizers to prolong thechemical and physical stability of formulated liquid agriculturalcompositions containing (i) one or more nitrification inhibitors, (ii)one or more urease inhibitors or (iii) a combination of both (i) and(ii). In one embodiment, the urease inhibitor is NBPT. In oneembodiment, the nitrification inhibitor is DCD.

There is also a need for improved NBPT formulations in DMSO to reducedecomposition of N-(n-butyl) thiophosphoric triamide (NBPT) intonon-effective substances. This decomposition can be observed throughcommon signs of degradation while undergoing long-term storage stabilitystudies. Specifically other side-products suspected of reacting withDMSO in formulation leaving large amounts of sediment and/or malodor inthe formulation generated while undergoing stability studies. The abovementioned disadvantages can be solved by adding a co-solvent to reduceNBPT degradation during a long-term storage resulting in unwantedsedimentation and/or odor masking agent to minimize any malodor in theformulation.

The present invention described herein will become apparent from thefollowing detailed description and examples, which comprises in oneaspect, a liquid composition for use in agricultural applicationscomprising: at least one of a nitrification inhibitor or a ureaseinhibitor; at least one solvent; and at least one stabilizer. In oneparticular embodiment, the at least one stabilizer is an aminestabilizer. In one embodiment, the liquid composition further comprisesa dye.

In one embodiment, the amine stabilizer is an alkanolamine. In anotherembodiment, the amine stabilizer is a monoalkanolamine. In anotherembodiment, the amine stabilizer is a dialkanolamine. In anotherembodiment, the amine stabilizer is a trialkanolamine. In yet anotherembodiment, the amine stabilizer is a monoethanolamine. In a furtherembodiment, the amine stabilizer is a diethanolamine. In yet a furtherembodiment, the amine stabilizer is a triethanolamine. In anotherembodiment, the alkanol group is chosen from methanol, ethanol,propanol, butanol. In one embodiment, the amine stabilizer is selectedfrom 2-amino-2-methyl-1-propanol, Amino-2-propanol, 2-Amino-1-butanol orany combination thereof.

In one embodiment, the amine stabilizer is 2-amino-2-methyl-1-propanol.In one embodiment, the amine stabilizer is Amino-2-propanol. In oneembodiment, the amine stabilizer is 2-Amino-1-butanol.

In another aspect, described herein are methods of making a solid orconcentrated liquid fertilizer compositions comprising treating (e.g.,contacting or spray applying) one or more nitrogenous fertilizercompounds with a liquid inhibitor composition. The liquid inhibitorcomposition comprises a nitrification inhibitor and/or a ureaseinhibitor, homogenously dissolved or dispersed in a solvent comprisingat least one amine stabilizer as described above. The liquid inhibitorcomposition, in one embodiment, further comprises at least one organicco-solvent selected from polar aprotic solvents, amine solvents,heterocyclic alcohol solvents, and mixtures thereof.

The term treating, in one embodiment, includes spray applying the liquidinhibitor composition with the one or more nitrogenous fertilizercompounds. The term treating, in one embodiment, includes but is notlimited to contacting the inhibitor composition with the one or morenitrogenous fertilizer compounds. In one embodiment, the nitrificationinhibitor is dicyandiamide (otherwise referred to herein as “DCD”). Inanother embodiment, the urease inhibitor is an alkyl thiophosphorictriamide.

In yet another aspect, described herein are concentrated liquidfertilizer compositions comprising, based on weight of the composition:(a) up to about 99 wt %, by weight of composition, of one or morenitrogenous fertilizer compounds, (b) at least one alkyl thiophosphorictriamide or an alkyl thiophosphoric triamide in combination withdicyandiamide, (c) at least one solvent as described herein and (d) atleast one amine stabilizer.

In a further aspect, described herein are concentrated liquid fertilizercompositions comprising, based on weight of the composition: (a) up toabout 99 wt %, by weight of composition, of one or more nitrogenousfertilizer compounds, (b) at least one of a dicyandiamide and/or analkyl thiophosphoric triamide, (c) optionally, at least oneorganophosphate compound according to formula (I.a), (d) at least onesolvent selected from polar aprotic solvents, heterocyclic alcoholsolvents, and mixtures thereof, (e) at least one amine stabilizer and(f) optionally, water. The concentrated liquid fertilizer compositionscan further comprise one or more stabilizers.

In yet another aspect, described herein are solid or substantially solidfertilizer compositions comprising: (a) solid particles of one or morenitrogenous fertilizer compounds, and (b) an inhibitor compositioncomprising at least one of a dicyandiamide or an alkyl thiophosphorictriamide supported on at least a portion of the solid particles. In oneembodiment, the inhibitor composition covers substantially all of thesolid particles. In one embodiment, evenly covers (or substantiallyevenly covers) all of the solid particles.

In another aspect, described herein are methods of making stable liquidor aqueous fertilizer composition comprising contacting one or morenitrogenous fertilizer compounds, with a liquid inhibitor compositionthat comprises at least one of a nitrification inhibitor or a ureaseinhibitor, homogenously dissolved or dispersed in a solvent comprisingat least one amine stabilizer. In one embodiment, the amine stabilizeris 2-amino-2-methyl-1-propanol. In one embodiment, the amine stabilizeris Amino-2-propanol. In one embodiment, the amine stabilizer is2-Amino-1-butanol. In one embodiment, the amine stabilizer ismonoethanolamine. The solvent can, optionally, further comprise anorganic co-solvent selected from polar aprotic solvents, amine solvents,heterocyclic alcohol solvents, and mixtures thereof.

In another aspect, the organophosphate compound has the formula (I.a)

wherein R₁, R₂ and R₃, are each independently chosen from H, a C₁-C₁₆alkyl group, a C₁-C₁₆ alkenyl, group, a C₁-C₁₆ alkoxyalkyl group, aC₇-C₃₀ alkylarylalkyl group, a C₇-C₃₀ arylalkyl group, or an aryl group;provided that at least one of R₁, R₂ or R₃ is not H. In anotherembodiment, R₁, R₂ and R₃, are each independently chosen from H, aC₁-C₁₂ alkyl group, a C₁-C₁₂ alkenyl, group, a C₁-C₁₂ alkoxyalkyl group,a C₇-C₃₀ alkylarylalkyl group, a C₇-C₃₀ arylalkyl group, or an arylgroup; provided that at least one of R₁, R₂ or R₃ is not H. In oneembodiment, R₁, R₂ and R₃, are each independently chosen from H, a C₁-C₄alkyl group, a C₄-C₈ alkyl group, a C₁-C₁₂ alkenyl, group, a C₁-C₄alkoxyalkyl group, a C₇-C₃₀ alkylarylalkyl group, a C₇-C₃₀ arylalkylgroup, or an aryl group; provided that at least one of R₁, R₂ or R₃ isnot H.

In yet another embodiment, R₁, R₂ and R₃, are each independently chosenfrom a C₁-C₁₂ alkyl group, a C₁-C₁₂ alkenyl, group, a C₁-C₁₂ alkoxyalkylgroup, a C₇-C₃₀ alkylarylalkyl group, a C₇-C₃₀ arylalkyl group, or anaryl group. In one embodiment, R₁, R₂ and R₃, are each independentlychosen from a C₁-C₁₂ alkyl group, more typically, a C₂-C₈ alkyl group.

In another aspect, described herein are methods for fertilizing targetplants, comprising applying an aqueous end use fertilizer compositionthat comprises: (a) one or more nitrogenous fertilizer compounds, (b) atleast one of a dicyandiamide or an alkyl thiophosphoric triamide,typically, alkyl thiophosphoric triamide, (c) at least one solventcomprising dimethyl sulfoxide, dimethyl formamide, monoethanolamine,amino-2-propanol, dimethylaminoethanol, triethanol amine, a heterocyclicalcohol according to formula (II.a):

or mixtures thereof, (d) an amine stabilizer, and optionally, (e) water,to the target plants or to an environment for the target plants. It isunderstood that the term heterocyclic alcohol includes dioxolanecompounds. The end use fertilizer composition can also comprise, in someembodiments, at least one stabilizer other than an amine stabilizer,which in one embodiment is an organophosphate compound.

In one embodiment, the alkyl thiophosphoric triamide isN-(n-butyl)-thiophosphoric triamide. In another embodiment, the liquidcomposition comprises dimethyl sulfoxide and at least one co-solventselected from the group consisting of: (a) at least one dioxolanecompound of formula (II.b):

wherein R₆ and R₇ individually comprises a hydrogen, an alkyl group, analkenyl group, or a phenyl group, wherein n is an integer of from 1 to10; b) at least one dibasic ester; c) at least one compound of formula(III):R₃OOC-A-CONR₄R₅  (III),wherein R3 comprises a C1-C36 alkyl group; wherein R4 and R5individually comprise a C1-C36 alkyl group, wherein R4 and R5 canoptionally together form a ring; and wherein A is a linear or a brancheddivalent C2-C12 alkyl group; d) at least one alkanolamine or alkoxylatedalkanolamine; e) at least one glycol or glycol derivative; f) at leastone organophosphate compound and g) any combination thereof.

In another aspect, the present invention is directed to a nitrificationinhibitor composition comprising dicyandiamide dissolved in a liquidmedium that comprises an organic solvent selected from polar aproticsolvents, dibasic esters, amines, amino alcohols, heterocyclic alcohols,and mixtures thereof.

In yet another aspect, the present invention is directed to a method ofmaking a solid or concentrated liquid fertilizer composition comprisingtreating (e.g., contacting, spray applying, brushing, etc) one or morenitrogenous fertilizer compounds with a nitrification inhibitorcomposition that comprises dicyandiamide dissolved in a liquid mediumthat comprises an organic solvent selected from polar aprotic solvents,amine solvents, heterocyclic alcohol solvents, and mixtures thereof.

In a further aspect, the present invention is directed to a concentratedliquid fertilizer composition comprising, by weight of the composition:

-   -   (a) up to about 99 wt % of one or more nitrogenous fertilizer        compounds,    -   (b) an alkyl thiophosphoric triamide or dicyandiamide (or a        combination thereof);    -   (c) at least one amine stabilizer;    -   (d) at least one solvent selected from polar aprotic solvents,        amine solvents, heterocyclic alcohol solvents, or mixtures        thereof, and    -   (d) optionally, water.

In another aspect, the present invention is directed to a concentratedsolid fertilizer composition comprising:

-   -   (a) solid particles of one or more nitrogenous fertilizer        compounds, and    -   (b) dicyandiamide or an alkyl thiophosphoric triamide supported        on at least a portion of the solid particles.

In one embodiment, the carrier utilized to contact the dicyandiamide oran alkyl thiophosphoric triamide with the solid particles comprises atleast one solvent as described herein and an amine stabilizer asdescribed herein.

In yet another aspect, the present invention is directed to a method ofmaking a stable, aqueous end use fertilizer composition comprisingcontacting one or more nitrogenous fertilizer compounds with a ureaseinhibitor composition that comprises an alkyl thiophosphoric triamidedissolved in a liquid medium that comprises an organic solvent selectedfrom polar aprotic solvents, amine solvents, heterocyclic alcoholsolvents, or mixtures thereof, in addition to an amine stabilizer.

In a further aspect, the present invention is directed to a method forfertilizing target plants, comprising applying an aqueous end usefertilizer composition that comprises:

-   -   (a) one or more nitrogenous fertilizer compounds;    -   (b) dicyandiamide, an alkyl thiophosphoric triamide, or a        mixture thereof;    -   (c) an amine stabilizer,    -   (d) at least one organic solvent;    -   (e) optionally, at least one dye, and    -   (f) optionally, water,    -   to the target plants or to an environment for the target plants.

DETAILED DESCRIPTION

As used herein, the term “alkyl” means a saturated straight chain,branched chain, or cyclic hydrocarbon radical, including but not limitedto, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, t-butyl,pentyl, n-hexyl, and cyclohexyl.

As used herein, the term “aryl” means a monovalent unsaturatedhydrocarbon radical containing one or more six-membered carbon rings inwhich the unsaturation may be represented by three conjugated doublebonds, which may be substituted one or more of carbons of the ring withhydroxy, alkyl, alkenyl, halo, haloalkyl, or amino, including but notlimited to, phenoxy, phenyl, methylphenyl, dimethylphenyl,trimethylphenyl, chlorophenyl, trichloromethylphenyl, am inophenyl, andtristyrylphenyl.

As used herein, the term “alkylene” means a divalent saturated straightor branched chain hydrocarbon radical, such as for example, methylene,dimethylene, trimethylene.

As used herein, the term “alkoxyl” means an oxy radical that issubstituted with an alkyl group, such as for example, methoxyl, ethoxyl,propoxyl, isopropoxyl, or butoxyl, which may optionally be furthersubstituted on one or more of the carbon atoms of the radical.

As used herein, the term “alkoxyalkyl” means an alkyl radical that issubstituted with one or more alkoxy substituents, more typically a(C₁-C₂₂)alkyloxy-(C₁-C₆)alkyl radical, such as methoxymethyl, andethoxybutyl.

As used herein, the term “alkenyl” means an unsaturated straight orbranched hydrocarbon radical, more typically an unsaturated straight,branched, (which, in one particular embodiment, is C₁-C₇₅) hydrocarbonradical, that contains one or more carbon-carbon double bonds, such as,for example, ethenyl, n-propenyl, iso-propenyl.

As used herein, the term “arylalkyl” means an alkyl group substitutedwith one or more aryl groups, more typically a (C₁-C₁₈)alkyl substitutedwith one or more (C₆-C₁₄)aryl substituents, such as, for example,phenylmethyl, phenylethyl, and triphenylmethyl.

As used herein, the term “aryloxy” means an oxy radical substituted withan aryl group, such as for example, phenyloxy, methylphenyl oxy,isopropylmethylphenyloxy.

As used herein, the terminology “(C_(r)-C_(s))” in reference to anorganic group, wherein r and s are each integers, indicates that thegroup may contain from r carbon atoms to s carbon atoms per group.

In one embodiment, non-limiting examples of nitrification inhibitorscomprise any one or more of N-2,5-dichlorophenyl succinamic acid,dicyandiamide (DCD), zinc ethylene-bis-dithiocarbamate,2,4,6-triehloroaniline, pentachlorophenol, thio-urea, ammoniumthiosulphate (ATS) or 3,4-dimethypyrazole phosphate (DMPP).

In one embodiment, non-limiting examples of urease inhibitors compriseany one or more of N-butyl thiophosphoric triamide (NBPT),N-(w-butyl)phosphoric triamide, miophosphoryl triamide, cyclohexylphosphoric triamide, cyclohexyl thiophosphoric triamide, phosphorictriamide, hydroquinone, p-benzoquinone, hexamidocyclotriphosphazene,thiopyridines, thiopyrimidines, thiopyridine-N-oxides,N,A′-dihalo-2-imidazolidinone, N-halo-2-oxazolidinone, ammoniumthiosulphate (ATS), N-cyclohexyl phosphoric triamide (CHPT), phenylphosphorodiamidate (PPT) and 2-nitrophenyl phosphoric triamide (2-NPT).

Dicyandiamide is a known compound according to formula (I.b):

Dicyandiamide, also known as “2-cyanoguanidine”, is typically made bytreating cyanamide with base and is commercially available.

In one embodiment, the compositions according to the present inventioncomprise a urease inhibitor, such as an alkyl thiophosphoric triamide orammonium thiosulfate, a nitrification inhibitor, or a combination ofboth a urease inhibitor and a nitrification inhibitor.

In one embodiment, alkyl thiophosphoric triamide isN-(n-butyl)-thiophosphoric triamide (“NBPT”). The at least one of alkylthiophosphoric triamide or dicyandiamide or combination thereof can bepresent in the liquid agricultural composition at a lower range of 2% byweight of the composition. In another embodiment, the at least one ofalkyl thiophosphoric triamide or dicyandiamide or combination thereofcan be present in the liquid agricultural composition at a lower rangeof 3% by weight of the composition. The at least one of alkylthiophosphoric triamide or dicyandiamide or combination thereof can bepresent in the liquid agricultural composition at a lower range of 5% byweight of the composition.

In another embodiment, at least one of urease inhibitor and/ornitrification inhibitor can be present in the liquid agriculturalcomposition at a lower range of 0.5%, or 1%, or 2%, or 3%, or 4%, or 5%,6%, or 8%, or 10% or 12% or 14%, by weight of the composition. Inanother embodiment, at least one of alkyl thiophosphoric triamide and/ordicyandiamide can be present in the liquid agricultural composition at alower range of 0.5%, or 1%, or 2%, or 3%, or 4%, or 5%, 6%, or 8%, or10% or 12% or 14%, by weight of the composition.

In another embodiment, the at least one urease inhibitor ornitrification inhibitor or combination thereof can be present in theliquid agricultural composition at an upper range of 75%, or 65%, or 60%by weight of the composition. In another embodiment, the at least one ofalkyl thiophosphoric triamide or dicyandiamide or combination thereofcan be present in the liquid agricultural composition at an upper rangeof 75%, or 65%, or 60% by weight of the composition. In anotherembodiment, the at least one of alkyl thiophosphoric triamide ordicyandiamide or combination thereof can be present in the liquidagricultural composition at an upper range of 60% by weight of thecomposition. In another embodiment, the at least one of alkylthiophosphoric triamide or dicyandiamide or combination thereof can bepresent in the liquid agricultural composition at an upper range of 55%by weight of the composition.

In another embodiment, the at least one urease inhibitor ornitrification inhibitor or combination thereof can be present in theliquid agricultural composition at an upper range of 59%, or 57%, or 55%or 53% or 50%, by weight of the composition. In another embodiment, atleast one of alkyl thiophosphoric triamide and/or dicyandiamide can bepresent in the liquid agricultural composition at an upper range of 59%,or 57%, or 55% or 53% or 50%, by weight of the composition.

In another embodiment, the at least one urease inhibitor ornitrification inhibitor or combination thereof can be present in theliquid agricultural composition at an upper range of 48%, or 46%, or 45%or 42% or 40%, by weight of the composition. In another embodiment, atleast one of alkyl thiophosphoric triamide and/or dicyandiamide can bepresent in the liquid agricultural composition at an upper range of 48%,or 46%, or 45% or 42% or 40%, by weight of the composition.

In another embodiment, the at least one of alkyl thiophosphoric triamideor dicyandiamide or combination thereof can be present in the liquidagricultural composition at an upper range of 35% by weight of thecomposition. In another embodiment, the at least one of alkylthiophosphoric triamide or dicyandiamide or combination thereof can bepresent in the liquid agricultural composition at an upper range of 30%by weight of the composition. In another embodiment, the at least one ofalkyl thiophosphoric triamide or dicyandiamide or combination thereofcan be present in the liquid agricultural composition at an upper rangeof 25% by weight of the composition.

In another embodiment, the at least one of alkyl thiophosphoric triamideor dicyandiamide can be present in the liquid agricultural compositionin an amount between about 7% by weight of the composition to about 55%by weight of the composition. In another embodiment, the at least one ofalkyl thiophosphoric triamide or dicyandiamide can be present in thecomposition in an amount between about 8% by weight of the compositionto about 50% by weight of the composition. In another embodiment, the atleast one of alkyl thiophosphoric triamide or dicyandiamide can bepresent in the liquid agricultural composition in an amount betweenabout 7% by weight of the composition to about 45% by weight of thecomposition. In another embodiment, the at least one of alkylthiophosphoric triamide or dicyandiamide can be present in the liquidagricultural composition in an amount between about 7% by weight of thecomposition to about 40% by weight of the composition. In anotherembodiment, the at least one of alkyl thiophosphoric triamide ordicyandiamide can be present in the liquid agricultural composition inan amount between about 7% by weight of the composition to about 35% byweight of the composition.

The at least one of alkyl thiophosphoric triamide or dicyandiamide canbe present in the composition in an amount between about 0.5% by weightof the composition and about 60% by weight of the composition or, inanother embodiment, can be present in the composition in an amountbetween about 1% by weight of the composition and about 40% by weight ofthe composition, and, in another embodiment, can be present in thecomposition in an amount between about 0.5% by weight of the compositionand about 20% by weight of the composition. In one particularembodiment, the at least one of alkyl thiophosphoric triamide ordicyandiamide is present in the composition in an amount between about1% by weight of the composition and about 30% by weight of thecomposition. The at least one of alkyl thiophosphoric triamide ordicyandiamide means that alkyl thiophosphoric triamide can be solelypresent, dicyandiamide can be solely present, or a combination of alkylthiophosphoric triamide and dicyandiamide is present.

The stabilizer can be any suitable amine compound. Compounds suitable asthe at least one amine stabilizer include alkanolamines and alkoxylatedalkanolamines. In one embodiment, the amine stabilizer is2-amino-2-methyl-1-propanol (sometimes referred to as “AMP”). In oneembodiment, the amine stabilizer is Amino-2-propanol. In one embodiment,the amine stabilizer is 2-Amino-1-butanol. In one embodiment, the aminestabilizer is a monoalkanolamine. In another embodiment, the aminestabilizer is a dialkanolamine. In another embodiment, the aminestabilizer is a trialkanolamine. In yet another embodiment, the aminestabilizer is a monoethanolamine. In a further embodiment, the aminestabilizer is a diethanolamine. In yet a further embodiment, the aminestabilizer is a triethanolamine. In another embodiment, the alkanolgroup is chosen from methanol, ethanol, propanol, butanol. In oneembodiment, the alkoxylate alkanolamine is an aminoalkoxy alcohol.

In one embodiment, the amine stabilizer is according to formula (IV):

wherein R₁ is H, CH₃, CH₂CH₃, or a branched or linear C₂-C₅ alkyl group,R₂ is H, CH₃, CH₂CH₃, or a branched or linear C₂-C₅ alkyl group, R₃ isH, CH₃ or a branched or linear C₂-C₅ alkyl group, and R₄ is H, CH₃ or abranched or linear C₂-C₅ alkyl group. In one embodiment, R₁ is CH₃, R₂is CH₃, R₃ is H, and R₄ is H. In another embodiment, R₁ is H, R₂ is H,R₃ is CH₃, and R₄ is H. In yet another embodiment, R₁ is CH₂CH₃, R₂ isH, R₃ is H, and R₄ is H.

In one embodiment, the amine stabilizer is 1,2-diaminocyclohexane (DCH)or Bis(hexamethylene)triamine (BHT). In another embodiment the aminestabilizer is selected from monoethanolamine, ethylaminoethanol,dimethylaminoethanol, isopropylaminoethanol, diethanolamine,triethanolamine, methylaminoethanol, am inopropanol,methylaminopropanol, dimethylaminopropanol, am inobutanol,dimethylaminobutanol, aminobutanediol, trihydroxymethylaminoethane,diethylaminopropanediol, 1-amino-cyclopentane methanol, and aminobenzylalcohol, or a heterocyclic ring that comprises at least one nitrogenatom as a ring member and/or is substituted on at least one carbon atomwith an amino group and that is substituted on at least one other carbonatom with a hydroxyalkyl or hydroxyl group, such asmethylaminomethyl-1,3-dioxolane.

The amine stabilizer component can form stable compositions whencombined with solvent compositions containing the nitrification and/orurease inhibitor, which in some embodiments means stability attemperatures ranging from −16° C. to 54° C., in other embodiments, −10°C. to 40° C., in other embodiments, −5° C. to 40° C., in otherembodiments, −2° C. to 40° C., or in other embodiments, 0° C. to 40° C.

In one embodiment, the stabilizer or amine stabilizer is present in theliquid composition in an amount between about 0.5% by weight of thecomposition to about 15% by weight of the composition. (It is understoodthat the term “%” can be used interchangeably with “wt %”)

In one embodiment, the stabilizer or amine stabilizer is present in theliquid composition at a lower range of 0.1%, or 0.2%, or 0.3%, or 0.4%,or 0.5%, or 0.6%, or 0.8%, or 1% or 1.2% or 1.4%, by weight of thecomposition. In one embodiment, the stabilizer or amine stabilizer ispresent in the liquid composition at a lower range of 1%, or 2%, or 3%,or 4%, or 5%, or 6%, or 7%, or 8%, or 10% by weight of the composition.

In one embodiment, the stabilizer or amine stabilizer is present in theliquid composition at an upper range of 10%, or 11%, or 12%, or 13%, or14%, or 15% by weight of the composition. In one embodiment, thestabilizer or amine stabilizer is present in the liquid composition atan upper range of 16%, or 18%, or 20%, or 22%, or 24%, or 26%, or 28%,or 30% by weight of the composition.

In another embodiment, compounds suitable as the organic solvent arepolar aprotic solvents, heterocyclic alcohol solvents, and/or mixturesthereof, that form liquid, or otherwise stable, compositions with thenitrification and/or urease inhibitor at temperatures at or greater than−16° C., in alternative embodiments, greater than −14° C., in otherembodiments, greater than −12° C., in other embodiments, greater than−10° C., in further embodiments, greater than −8° C., in otherembodiments, greater than −5° C., in other embodiments, greater than −3°C., in other embodiments, greater than −2° C., in other embodiments,greater than 0° C., in other embodiments, greater than 2° C., in otherembodiments, greater than 4° C., in other embodiments, greater than 5°C.

In some embodiments, at high temperature ranges or at greater than aspecified temperature (as described herein), the liquid fertilizercomposition is stable, meaning the urease and/or nitrificationinhibitor(s) do not react with the solvent or solvent component underanticipated manufacturing, storage, and use conditions. In oneembodiment, the liquid fertilizer compositions are stable at atemperature greater than 25° C. In one embodiment, the liquid fertilizercompositions are stable at a temperature greater than 27° C. In oneembodiment, the liquid fertilizer compositions are stable at atemperature greater than 29° C. In one embodiment, the liquid fertilizercompositions are stable at a temperature greater than 30° C. In oneembodiment, the liquid fertilizer compositions are stable at atemperature greater than 32° C. In one embodiment, the liquid fertilizercompositions are stable at a temperature greater than 34° C. In oneembodiment, the liquid fertilizer compositions are stable at atemperature greater than 35° C. In one embodiment, the liquid fertilizercompositions are stable at a temperature greater than 37° C. In oneembodiment, the liquid fertilizer compositions are stable at atemperature greater than 40° C. In one embodiment, the liquid fertilizercompositions are stable at a temperature greater than 42° C. In oneembodiment, the liquid fertilizer compositions are stable at atemperature greater than 44° C. In one embodiment, the liquid fertilizercompositions are stable at a temperature greater than 45° C. In oneembodiment, the liquid fertilizer compositions are stable at atemperature greater than 47° C. In one embodiment, the liquid fertilizercompositions are stable at a temperature greater than 50° C.

In one embodiment, at the specified temperature ranges or at greaterthan a specified temperature (as described herein), the liquidfertilizer composition is stable, meaning the liquid fertilizercomposition is or substantially is in one phase, i.e., no visiblecrystals, no visible precipitation, and/or no visible multiple liquidphases. In another embodiment, the liquid fertilizer composition isstable, meaning the liquid fertilizer composition is or substantially isin one phase and shows little or slight discoloration.

In one embodiment, the liquid fertilizer composition is stable, meaningthat the co-solvent does not degrade or chemically react to othercomponents in the composition.

In one embodiment, the liquid fertilizer compositions contains anorganophosphate compound according to formula (I.a) (wherein R₁, R₂ andR₃ are as described above).

Suitable polar aprotic organic solvents include, for example,dichloromethane, dimethyl acetamide, dimethyl formamide, dimethylsulfoxide, ethyl acetate, hexamethylphosphoramide, dimethyl sulfone,sulfolane, 1,3-dimethyl-2-imidazoidinone,1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone, methyl acetate, ethyllactate, methylpyrrolidone, tetrahydrofuran, propylene carbonate, anddibasic ester solvents.

Suitable dibasic ester solvents include, for example, dialkyl esters ofdicarboxylic acids, more typically, the di(C₁-C₁₂)alkyl esters ofsaturated linear or branched (C₂-C₈)aliphatic carboxylic acids or amixture thereof. In one embodiment, the dibasic ester componentcomprises one or more compounds according to formula (III):R¹OOC-A-CONR²R³  (III)wherein:

-   -   A is a divalent linear or branched (C₂-C₈)aliphatic group, and    -   R¹, R², and R³ are each independently (C₁-C₁₂)alkyl,        (C₁-C₁₂)aryl, (C₁-C₁₂)alkaryl or (C₁-C₁₂)arylalkyl, and R² and        R³ may each optionally be substituted with one or more hydroxyl        groups.

Glycols and glycol derivatives include but are not limited to aliphaticdihydroxy (dihydric) alcohols. In one embodiment, glycol derivativesinclude but are not limited to polypropylene glycol, triethylene glycol,glycol alkyl ethers such as dipropylene glycol methyl ether, diethyleneglycol. In another embodiment, glycol derivatives include but are notlimited to polyglycols such as polyethylene glycols (PEG) andpolypropylene glycols. Glycols are represented by the general formulaC_(n)H2_(n)(OH)₂, where n is at least 2. Non-limiting examples ofglycols include ethylene glycol (glycol), propylene glycol(1,2-propanediol), 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol,1,7-heptanediol, 1,9-nonanediol, 1,10-decanediol, 1,8-octanediol,1,3-propanediol, 1,3-butanediol, 1,4-butanediol, 2,3-butanediol,2,4-pentanediol, 2,5-hexanediol, 4,5-octanediol and 3,4-hexanediol,neopenty glycol, pinacol, 2,2-diethyl-1,3-propanediol,2-ethyl-1,3-hexanediol, 2-ethyl-2-butyl-1,3-propanediol, isobutyleneglycol, 2,3-dimethyl-1,3-propanediol, 1,3-diphenyl-1,3-propanediol,3-methyl-1,3-butanediol.

In another embodiment, glycol derivatives include but are not limited toglycol stearate, ethylene glycol monostearate, ethylene glycoldistearate, ethylene glycol amido stearate, dilaurate glycol, propyleneglycol monostearate, propylene glycol dicaprylate, propylene glycoldicaprate diacetate glycol, dipalmite glycol, diformate glycol,dibutyrate glycol, dibenzorate glycol, dipalmate glycol, dipropionateglycol, monoacetate glycol, monopalmitate glycol and monoformate glycol.In another embodiment, glycol derivatives also include polypropyleneglycol, triethylene glycol, dipropylene glycol methyl ether, ordiethylene glycol.

Polyglycol derivatives include but are not limited to polyethyleneglycol (PEG) 200-6000 mono and dilaurates, such as, PEG 600 dilaurate,PEG 600 monolaurate, PEG 1000 dilaurate, PEG 1000 monolaurate, PEG 1540dilaurate and PEG 1540 monolaurate, polyethylene glycol 200-6000 monoand dioleates, such as, PEG 400 monoleate, PEG 600 dioleate, PEG 600monooleate, PEG 1000 monoleate, PEG 1540 dioleate, PEG 1540 monooleateand polyethylene glycol 200-6000 mono and distearates, such as, PEG 400distearate, PEG 400 monostearate, PEG 600 distearate, PEG 600monostearate, PEG 1000 distearate, PEG 1000 monostearate, PEG 1540distearate, PEG 1540 monostearate and PEG 3000 monostearate.

Examples of glycerol derivatives include but are not limited to glycerolmonolaurate, glycerol monostearate, glycerol distearate, glyceroltrioleate, glycerol monooleate, glycerol dilaurate, glyceroldipalmitate, glycerol triacetate, glycerol tribenzoate, glyceroltributyrate, glycerol monopalmitate, glycerol trimyristate, glyceroltrilaurate, glycerol tripalmitate and glycerol tristearate.

Suitable heterocyclic alcohol solvents include, for example, 5- or6-membered heterocyclic rings that include 1 or 2 oxygen atoms as ringmember, that are substituted on at least one carbon atom of the ringwith a (C₁-C₆)hydroxyalkyl group, and that may optionally be substitutedon one or more carbon atoms of the ring with one or more (C₁-C₄)alkylgroups. It is understood that the term heterocyclic alcohol includesdioxolane compounds. In one embodiment, the heterocyclic alcoholcomponent of the present invention comprises a one or more compoundsselected from heterocyclic alcohols according to formulas (II.c),(II.d), (II.e), (II.f), and (II.g):

In one embodiment, the organic solvent component comprises one or moredibasic ester compounds, one or more amino alcohols, one or moretertiary amines, one or more heterocyclic alcohols according to formulas(II.a-II.g), or mixtures thereof.

In one embodiment, the organic solvent component of the composition andmethods of the present invention comprises dimethyl sulfoxide,monoethanolamine, methyl-5-(dimethylamino)-2-methyl-oxopentanoate,dimethylaminoethanol, triethanol amine, a heterocyclic alcohol accordingto any of formulas (II.a-II.g), or a mixture thereof.

In one embodiment, the organic solvent component of the composition andmethods of the present invention comprises a mixture of at least oneorganophosphate solvent according to formula (I.a), wherein R₁, R₂ andR₃ are as described above.

In one embodiment, a compound utilized as the solvent or as a componentin the solvent blend is a compound of general formula (III):R₃OOC-A-CONR₄R₅  (III),

According to one embodiment, the expression “compound” denotes anycompound corresponding to the general formula (III). In otherembodiments, the term “compound” also refers to mixtures of severalmolecules corresponding to general formula (III). It may therefore be amolecule of formula (III) or a mixture of several molecules of formula(III), wherein both fall under the definition of the term “compound”when referring to formula (III).

The R₃, R₄ and R₅ groups can be, in some embodiments, identical or, inother embodiment, different. In one embodiment, may be groups chosenfrom C₁-C₂₀ alkyl, aryl, alkaryl or arylalkyl groups or the phenylgroup. In another embodiment, may be groups chosen from C₁-C₁₂ alkyl,aryl, alkaryl or arylalkyl groups or the phenyl group. Mention is madeespecially of Rhodiasolv® PolarClean (Manufactured by Solvay USA Inc.,Princeton, N.J.). The R₄ and R₅ groups may optionally be substituted. Inone particular embodiment, the groups are substituted with hydroxylgroups.

In one embodiment, R₃ group is chosen from methyl, ethyl, propyl,isopropyl, n-butyl, isobutyl, n-pentyl, isopentyl, isoamyl, n-hexyl,cyclohexyl, 2-ethylbutyl, n-octyl, isooctyl, 2-ethylhexyl, tridecylgroups.

R₄ and R₅ groups, which are identical or different, in one embodiment,may especially be chosen from methyl, ethyl, propyl (n-propyl),isopropyl, n-butyl, isobutyl, n-pentyl, amyl, isoamyl, hexyl, cyclohexylor hydroxyethyl groups. The R₄ and R₅ groups may also be such that theyform, together with the nitrogen atom, a morpholine, piperazine orpiperidine group. According to some embodiments, R₄ and R₅ are eachmethyl, or R₄ and R₅ are each ethyl, or R₄ and R₅ are each hydroxyethyl.

According to one embodiment, if A comprises a linear group of formula—CH₂—CH₂— and/or of formula —CH₂— CH₂— CH₂— CH₂— and/or of formula—(CH₂)₈— then it is a mixture of A groups. According to one particularembodiment, if A is linear, then it is a mixture of A groups, forexample a mixture of two or three —CH₂— CH₂— (ethylene); —CH₂— CH₂— CH₂—(n-propylene); and —CH₂— CH₂— CH₂— CH₂— (n-butylene) groups (or isomersthereof).

According to a first particular embodiment of the invention, the A groupis a divalent linear alkyl group chosen from the groups of the followingformulae: —CH₂—CH₂— (ethylene); —CH₂— CH₂— CH₂— (n-propylene); —CH₂—CH₂— CH₂— CH₂— (n-butylene), and mixtures thereof.

Suitable Odor Masking Agents include but are not limited to methylacetate, ethyl acetate, cyclohexyl acetate, benzyl acetate, isoamylacetate, geranyl acetate, hexyl acetate, octyl acetate, phenylethylacetate, methyl butyrate, ethyl butyrate, 2-methylbutyl butyrate,isoamyl butyrate, methyl formate, methyl propionate, pentyl butyrate,2-methylbutyl 2-methylbutyrate, ethyl methylphenylglycidate, dimethylphthalate, or diethyl malonate.

Suitable Odor Masking Agents include but are not limited to: citral,citronellol, camphor, cedrene, carvone, dipentene, eucalyptol, geraniol,α-ionone, linalool, limonene, menthol, myrcene, neral, nerolidol,α-pinene, β-pinene, α-phellandrene, β-phellandrene, terpineol,α-terpinene, β-terpinene, or thujone.

Suitable Odor Masking Agents include but are not limited to:acetaldehyde, anisic aldehyde, benzaldehyde, butyraldehyde,cinnamaldehyde, capraldehyde, cuminaldehyde, decanal, hexanal, hexylcinnamaldehyde, isomenthone, isovaleraldehyde, menthone, propionaldehydeor valeraldehyde.

Suitable Odor Masking Agents include but are not limited to: benzylalcohol, cis-3-hexen-1-ol, furaneol, 1-hexanol, phenylethyl alcohol;4-allylanisole, anisole, anethole, eugenol, γ-decalactone,γ-nonalactone, thymol dihydrojasmone, vanillin, mint, oil Japanesecherry or lactones

In one embodiment, the Odor Masking Agent is chosen from at least one ofIsoamyl butyrate, 4-Allylanisole, Limonene, Terpineol, terpenes,4-(2,6,6-Trimethyl-2-cyclohexenyl)-3-buten-2-one, Benzaldehyde, DiethylMalonate, Cyclohexyl acetate, Anisole, α-Ionone, mint, oil Japanesecherry and rose ketones. In one embodiment, the Odor Masking Agent isisoamyl butyrate. In some embodiments, an amount of less than 5 wt % (bytotal weight of composition) of odor masking agent is added to thecomposition. In some embodiments, an amount of less than 3 wt % (bytotal weight of composition) of odor masking agent is added to thecomposition. In some embodiments, an amount of less than 2 wt % (bytotal weight of composition) of odor masking agent is added to thecomposition. In some embodiments, an amount of less than 1 wt % (bytotal weight of composition) of odor masking agent is added to thecomposition. In some embodiments, an amount of less than about 1.6 wt %(by total weight of composition) of odor masking agent is added to thecomposition. In some embodiments, an amount of from 1 wt % to 3 wt % ofthe odor masking agent (for example, isoamyl butyrate) is added to theliquid formulations of the present invention. These formulations areimparted with stability in assay, flash point, and cold temperature forup to 12 weeks at room temperature and 45° C. The overall odor of theliquid compositions containing DMSO, for example, were significantlyimproved.

Examples of suitable dyes include but are not limited to any one or moreof: Carbon Black, Pigment Blue 15, Pigment Blue 15:1, Pigment Blue 15:2,Pigment Blue 15:3, Pigment Blue 15:4, Pigment Blue 15:6, Pigment Blue 1,Pigment Blue 10, Pigment Blue 14, Pigment Blue 60, Pigment Blue 61,Pigment Yellow 1, Pigment Yellow 3, Pigment Yellow 12, Pigment Yellow13, Pigment Yellow 14, Pigment Yellow 17, Pigment Yellow 24, PigmentYellow 55, Pigment Yellow 62, Pigment Yellow 63, Pigment Yellow 65,Pigment Yellow 73, Pigment Yellow 74, Pigment Yellow 81, Pigment Yellow83, Pigment Yellow 93, Pigment Yellow 95, Pigment Yellow 97, PigmentYellow 110, Pigment Yellow 111, Pigment Yellow 123, Pigment Yellow 126,Pigment Yellow 127, Pigment Yellow 139, Pigment Yellow 147, PigmentYellow 150, Pigment Yellow 151, Pigment Yellow 154, Pigment Yellow 155,Pigment Yellow 168, Pigment Yellow 170, Pigment Yellow 174, PigmentYellow 175, Pigment Yellow 176, Pigment Yellow 179, Pigment Yellow 180,Pigment Yellow 183, Pigment Yellow 185, Pigment Yellow 188, PigmentYellow 191, Pigment Yellow 194, Pigment Yellow 214, Pigment Red 2,Pigment Red 3, Pigment Red 4, Pigment Red 5, Pigment Red 8, Pigment Red9, Pigment Red 12, Pigment Red 13, Pigment Red 21, Pigment Red 22,Pigment Red 23, Pigment Red 31, Pigment Red 32, Pigment Red 48:1,Pigment Red 48:2, Pigment Red 48:3, Pigment Red 48:4, Pigment Red 49:1,Pigment Red 49:2, Pigment Red 52:1, Pigment Red 52:2, Pigment Red 53:1,Pigment Red 53:3, Pigment Red 57:1, Pigment Red 63:1, Pigment Red 81,Pigment Red 112, Pigment Red 122, Pigment Red 123, Pigment Red 144,Pigment Red 146, Pigment Red 149, Pigment Red 166, Pigment Red 169,Pigment Red 170, Pigment Red 171, Pigment Red 175, Pigment Red 176,Pigment Red 177, Pigment Red 178, Pigment Red 179, Pigment Red 184,Pigment Red 185, Pigment Red 188, Pigment Red 189, Pigment Red 202,Pigment Red 208, Pigment Red 210, Pigment Red 224. Pigment Red 242,Pigment Red 245, Pigment Red 254, Pigment Red 266, Pigment Red 268,Pigment Red 269, Pigment Orange 5, Pigment Orange 13, Pigment Orange 16,Pigment Orange 34, Pigment Orange 36, Pigment Orange 63, Pigment Violet1, Pigment Violet 2, Pigment Violet 3, Pigment Violet 19, Pigment Violet23, Pigment Violet 27, Pigment Green 7, Pigment Green 36, and the like.Suitable dyes include but are not limited to Yellow #5 Aluminum dye lake(SunCROMA), LITHOL Fast Yellow 0991K (BASF); PALIOTOL Yellow 1840(BASF); NOVOPERM Yellow FGL (Clariant); FD&C Yellow 5 AI Lake(SunCROMA), PALIOGEN Violet 5100 (BASF); PALIOGEN Violet 5890 (BASF);HELIOGEN Green L8730 (BASF); LITHOL Scarlet D3700 (BASF); SUNFAST Blue15:4 (Sun Chemical); Permanent Red P-F7RK; Hostaperm Violet BL(Clariant); LITHOL Scarlet 4440 (BASF); Bon Red C (Dominion ColorCompany); ORACET Pink RF (BASF); PALIOGEN Red 3871K (BASF); NEOPEN BlueFF4012 (BASF); PV Fast Blue B2GO1 (Clariant); IRGALITE Blue BCA (BASF);SUNFAST Blue 15:3 (Sun Chemical); PALIOGEN Red 3340 (BASF); SUNFASTCarbazole Violet 23 (Sun Chemical); LITHOL Fast Scarlet L4300 (BASF);SUNBRITE Yellow 17 (Sun Chemical); HELIOGEN Blue L6900, L7020 (BASF);SUNBRITE Yellow 74 (Sun Chemical); SPECTRA PAC C Orange 16 (SunChemical); Hostaperm Blue B2G-D (Clariant); HELIOGEN Blue K6902, K6910(BASF); SUNFAST Magenta 122 (Sun Chemical); HELIOGEN Blue D6840, D7080(BASF); Sudan Blue OS (BASF); PALIOGEN Blue 6470 (BASF); Tartrazineyellow dye (ORCO), Sudan Orange G (Aldrich), Sudan Orange 220 (BASF);Milliken Liquitint Agro Green ZA 6040, Milliken Green #6-ExperimentalGreen MM04201703A, Milliken Green #7-Experimental Green MM01201724A,ORCO Blue SI-MC/ORCO Yellow, PALIOGEN Orange 3040 (BASF); PALIOGENYellow 152, 1560 (BASF); Lumogen Yellow D0790 (BASF); Suco-Yellow L1250(BASF); Suco-Yellow D1355 (BASF); Suco Fast Yellow DI 355, DI 351(BASF); HOSTAPERM Pink E 02 (Clariant); Hansa Brilliant Yellow 5GX03(Clariant); Permanent Yellow GRL 02 (Clariant); Permanent Rubine L6B 05(Clariant); FANAL Pink D4830 (BASF); CINQUASIA Magenta (DU PONT);PALIOGEN Black L0084 (BASF); Pigment Black K801 (BASF); and carbonblacks such as REGAL 330™ (Cabot), Carbon Black 5250, Carbon Black 5750(Columbia Chemical), as well as mixtures thereof and the like. In otherembodiments, additional components, such as odor masking agents can beadded to the composition.

In one embodiment, the dye is present in the composition at a lowerrange of about 0.05%, or 0.1%, or 0.15%, or 0.2%, or 0.25%, or 0.3%, or0.35%, or 0.4% by weight of the composition. In one embodiment, the dyeis present in the composition at a lower range of about 0.1%, or 0.2%,or 0.3%, or 0.4%, or 0.5%, or 0.6%, or 0.7%, or 0.8%, or 1% by weight ofthe composition.

In one embodiment, the dye is present in the composition at an upperrange of about 0.8%, or 0.9%, or 1%, or 1.1%, or 1.2%, or 1.3% by weightof the composition. In one embodiment, the dye is present in thecomposition at an upper range of about 1%, or 2%, or 3%, or 4%, or 5% byweight of the composition.

In one embodiment, the inhibitor composition of the present inventioncomprises, based upon total weight of the composition:

from about 4 wt % to about 60 wt %, more typically from about 10 wt % toabout 55 wt %, which in one embodiment is NBPT;

from about 55 wt % to about 96 wt %, more typically from about 58 wt %to about 90 wt %, and even more typically from about 60 wt % to about 80wt % of at least one organic solvent;

from about 0.1 wt % to about 20 wt %, more typically from about 1 wt %to about 10 wt %, even more typically from about 1 wt % to about 5 wt %of at least one amine stabilizer and

from about 0.01 wt % to about 8 wt %, more typically from about 0.1 wt %to about 5 wt %, even more typically from about 0.1 wt % to about 3 wt %of at least one dye.

In one embodiment, the inhibitor composition of the present inventioncomprises, based upon total weight of the composition, from about 0.1 wt% to about 20 wt %, more typically from about 1 wt % to about 10 wt %,even more typically from about 1 wt % to about 5 wt % of at least oneamine stabilizer; and

In one embodiment, the inhibitor composition of the present inventioncomprises, based on 100 parts by weight (“pbw”) of the composition:

from about 4 to about 60 pbw, more typically from about 10 to about 55pbw, and even more typically from about 20 to about 40 pbw of a ureaseinhibitor, which in one embodiment is NBPT;

from about 55 to about 96 pbw, more typically from about 58 to about 90pbw, and even more typically from about 60 to about 80 pbw of theorganic solvent;

from about 0.5 to about 20 pbw, more typically from about 1 to 10 pbw,even more typically from about 1 to about 5 pbw of the amine stabilizer;and from about 0.01 to about 8 pbw, more typically from about 0.1 to 5pbw, even more typically from about 0.1 to about 3 pbw of the dye.

In one embodiment, the inhibitor composition of the present inventioncomprises one or more urease inhibitors, such as, for example, NBPT orammonium thiosulfate. In one embodiment, the inhibitor composition asdescribed herein comprises one or more nitrification inhibitors, suchas, for example DCD.

The nitrogenous fertilizer compound is treated with the inhibitorcomposition by contacting the nitrogenous fertilizer composition withthe inhibitor composition described herein (e.g., nitrificationinhibitor or urease inhibitor or a combination of both). The nitrogenousfertilizer composition may be in solid or liquid form.

Suitable nitrogenous fertilizers are those containing a nitrogenouscompound such as urea, nitrate salts, ammonium salt, or a mixturethereof, such as ammonium nitrate, ammonium sulfate, ammoniumthiosulfate, ammonium polysulfide, ammonium phosphates, ammoniumchloride, ammonium bicarbonate, anhydrous ammonia, calcium nitrate,nitrate soda, calcium cyanamide. In one embodiment, the nitrogenousfertilizer comprises ammonium nitrate. Suitable ammoniumnitrate-containing fertilizers include, for example, UAN 18, UAN 28, andUAN 30.

In one embodiment, the nitrogenous fertilizer composition is in solidparticulate form, and the contacting of the nitrogenous fertilizercomposition with the inhibitor composition is conducted by, for example,spraying the composition of the present invention on the particles ofsolid fertilizer composition.

Methods of stabilizing a liquid fertilizer composition comprisecontacting 1) an amine stabilizer as described herein with 2) a liquidinhibitor composition that comprises one or more nitrogenous fertilizercompounds and at least one of a dicyandiamide or an alkyl thiophosphorictriamide, which is dissolved or dispersed in a liquid medium. The liquidmedium, in some embodiments comprise: dimethylfulfoxide and at least oneco-solvent selected from: (a) a dioxolane compound of formula (II.b)[described above], (b) at least one compound of formula (III) [describedabove], (c) at least one compound according to formula (I.a) [describedabove], or (d) a glycol or glycol derivative

In one embodiment, the concentrated fertilizer composition of thepresent invention is a solid nitrification-inhibited fertilizercomposition that comprises, based on 100 pbw of the composition:

from about 60 pbw to about 99.999, more typically from about 70 pbw toabout 99.999, and even more typically from about 80 pbw to about 99.999solid particles of one or more nitrogenous fertilizer compounds, and

from about 0.001 to about 40 pbw, more typically from about 0.001 toabout 30 pbw, and even more typically from about 0.001 to about 20 pbw,a urease inhibitor or a nitrification inhibitor.

In one embodiment, the solid nitrification-inhibited fertilizercomposition of the present invention further comprises one or moreurease inhibitors, more typically NBPT.

In one embodiment, the fertilizer compound is in liquid form and thecontacting of the fertilizer composition with the inhibitor compositionis conducted by mixing the inhibitor composition with the liquidfertilizer composition.

In one embodiment, the concentrated fertilizer composition of thepresent invention is a concentrated liquid nitrification-inhibitedfertilizer composition that comprises, based on 100 pbw of thecomposition:

from about 20 to about 99.989 pbw, more typically from about 30 to about99.985 pbw, and even more typically from about 40 to about 99.98 pbw ofone or more nitrogenous fertilizer compounds,

from about 0.001 to 40 pbw, more typically from about 0.005 to 30 pbw,and even more typically from about 0.01 to 20 pbw urease inhibitor(e.g., NBPT), a nitrification inhibitor (e.g., DCD) or a combinationthereof (e.g., NBPT in combination with DCD), and

from about 0.01 to 60 pbw, more typically from about 0.01 to about 40pbw, and even more typically from about 0.01 to about 30 pbw of theorganic solvent or solvent mixture, as described herein.

In one embodiment, the concentrated liquid nitrification-inhibitedfertilizer composition of the present invention further comprises one ormore urease inhibitors, more typically NBPT.

In one embodiment, the end use fertilizer composition of the presentinvention is made by combining the inhibitor composition of the presentinvention with a concentrated nitrogenous fertilizer to form aconcentrated liquid nitrification-inhibited fertilizer composition andsubsequently diluting the concentrated liquid nitrification-inhibitedfertilizer composition with an aqueous medium, typically water in aratio of up to about 500 pbw, more typically from about 10 to about 500pbw and even more typically from about 100 to about 300 pbw, of theaqueous medium per 1 pbw concentrated liquid nitrogenous fertilizercomposition.

In one embodiment, the end use fertilizer composition of the presentinvention is made by combining the inhibitor composition of the presentinvention, a solid or concentrated liquid nitrogenous fertilizer, and anaqueous medium.

In one embodiment, the end use fertilizer composition of the presentinvention comprises one or more urease inhibitors, more typically NBPT,alone or in combination with the nitrification inhibitor.

In one embodiment, the end use fertilizer composition of the presentinvention comprises from about 0.001 to about 5 pbw, more typically fromabout 0.01 to about 2 pbw urease inhibitor and/or nitrificationinhibitor per 100 pbw of the one or more nitrogenous fertilizercompounds.

In one embodiment, the end use fertilizer composition is applied totarget plants or to an environment for the target plants, i.e., toground on or within which the target plants are growing or to be grown,at a rate of from about 0.01 pounds to about 5 pounds of the fertilizercomposition, more typically from about 0.05 pounds to about 2 pounds ofthe fertilizer composition, per 100 square feet of ground.

In one embodiment, the end use fertilizer composition is applied totarget plants or to an environment for the target plants at a rateeffective to provide a dosage of nitrogenous fertilizer compound of fromabout 0.01 pounds to about 5 pounds of fertilizer compound, moretypically from about 0.05 pounds to 2 pounds of fertilizer compound, per100 square feet of ground.

In one embodiment, the end use fertilizer composition is applied totarget plants or to an environment for the target plants at a rateeffective to provide a dosage of fertilizer of from about 0.01 pounds to5 pounds of fertilizer, more typically from about 0.05 pounds to 2pounds of fertilizer, per 1000 square feet of ground.

The composition of the present invention provides improved ease ofhandling of urease inhibitors and/or nitrification inhibitors, improvedsolubility characteristics, low toxicity of the organic solvents; goodstorage characteristics, and excellent miscibility with aqueouscompositions, such as aqueous nitrogenous fertilizer formulations.

In one embodiment the composition comprises, by weight of composition,greater than 50 wt % of a urease inhibitor (e.g., NBPT), nitrificationinhibitor (e.g., DCD), or a combination thereof, the remainder being atleast solvent or a mixture of solvents, amine stabilizer and a dye. Byway of example, in one embodiment, the fertilizer composition comprises,by weight of composition:

at least 50 wt % of a urease inhibitor (e.g., NBPT), nitrificationinhibitor (e.g., DCD), or a combination thereof and

less than or equal to 50 wt % of a solvent blend, at least one aminestabilizer and, optionally, a dye.

In one embodiment the composition comprises, by weight of composition,greater than 25 wt % of a urease inhibitor (e.g., NBPT), nitrificationinhibitor (e.g., DCD), or a combination thereof, the remainder being atleast solvent or a mixture of solvents, amine stabilizer and a dye. Byway of example, in one embodiment, the fertilizer composition comprises,by weight of composition:

at least 25 wt % of a urease inhibitor (e.g., NBPT), nitrificationinhibitor (e.g., DCD), or a combination thereof and

less than or equal to 75 wt % of a solvent blend, at least one aminestabilizer and, optionally, a dye. In one embodiment, the solvent blendcomprises DMSO.

In one embodiment the stable liquid agricultural composition comprises,by weight of composition,

greater than 25 wt % of a urease inhibitor;

a solvent blend comprising a) a mixture of triethylene glycol and b) atleast one compound of formula (III):R₃OOC-A-CONR₄R₅  (III),

wherein R₃ comprises a C₁-C₃₆ alkyl group; wherein R₄ and R₅individually comprise a C₁-C₃₆ alkyl group, wherein R₄ and R₅ canoptionally together form a ring; and wherein A is a linear or a brancheddivalent C₂-C₁₂ alkyl group; and

optionally, a dye

In one embodiment the stable liquid agricultural composition comprises,by weight of composition,

greater than 25 wt % of a urease inhibitor;

a solvent blend comprising a) a mixture of triethylene glycol and b)propylene glycol; and

optionally, a dye.

In one embodiment the stable liquid agricultural composition comprises,by weight of composition:

less than 30 wt % of a urease inhibitor;

a solvent blend comprising a) a glycol derivative and b) at least onecompound of formula (III):R₃OOC-A-CONR₄R₅  (III),

wherein R₃ comprises a C₁-C₃₆ alkyl group; wherein R₄ and R₅individually comprise a C₁-C₃₆ alkyl group, wherein R₄ and R₅ canoptionally together form a ring; and wherein A is a linear or a brancheddivalent C₂-C₁₂ alkyl group;

optionally, a dye; and

optionally, an odor masking agent.

In one embodiment, the glycol derivative is triethylene glycol.

In one embodiment the stable liquid agricultural composition comprises,by weight of composition:

less than 30 wt % of a urease inhibitor;

a solvent blend comprising a mixture of glycol derivatives;

optionally, a dye; and

optionally, an odor masking agent.

The mixture of glycol derivatives can comprise, in one embodiment,triethylene glycol and propylene glycol.

In one embodiment the composition comprises, by weight of composition,greater than 50 wt % of a urease inhibitor such as NBPT, the remainderbeing solvent or a mixture of solvents with the amine stabilizer. In oneembodiment the composition comprises, by weight of composition, greaterthan 51 wt %, 52 wt %, 53 wt %, 54 wt % of a urease inhibitor such asNBPT, the remainder being solvent or a mixture of solvents with theamine stabilizer. In one embodiment the composition comprises, by weightof composition, greater than 55 wt %, 56 wt %, 57 wt %, 58 wt %, 59 wt %a urease inhibitor such as of NBPT, the remainder being solvent or amixture of solvents with the amine stabilizer. In one embodiment thecomposition comprises, by weight of composition, greater than 60 wt % ofa urease inhibitor such as NBPT, the remainder being solvent or amixture of solvents with the amine stabilizer. In one embodiment thecomposition comprises, by weight of composition, greater than 65 wt % ofa urease inhibitor such as NBPT, the remainder being solvent or amixture of solvents with the amine stabilizer. In one embodiment thecomposition comprises, by weight of composition, greater than 70 wt % ofa urease inhibitor such as NBPT, the remainder being solvent or amixture of solvents with the amine stabilizer. In one embodiment thecomposition comprises, by weight of composition, greater than 75 wt % ofa urease inhibitor such as NBPT, the remainder being solvent or amixture of solvents with the amine stabilizer.

In one embodiment the composition comprises, by weight of composition,greater than 50 wt % of a nitrification inhibitor such as DCD, theremainder being solvent or a mixture of solvents with the aminestabilizer. In one embodiment the composition comprises, by weight ofcomposition, greater than 51 wt %, 52 wt %, 53 wt %, 54 wt % of anitrification inhibitor such as DCD, the remainder being solvent or amixture of solvents with the amine stabilizer. In one embodiment thecomposition comprises, by weight of composition, greater than 55 wt %,56 wt %, 57 wt %, 58 wt %, 59 wt % of a nitrification inhibitor such asDCD, the remainder being solvent or a mixture of solvents with the aminestabilizer. In one embodiment the composition comprises, by weight ofcomposition, greater than 60 wt % of a nitrification inhibitor such asDCD, the remainder being solvent or a mixture of solvents with the aminestabilizer. In one embodiment the composition comprises, by weight ofcomposition, greater than 65 wt % of a nitrification inhibitor such asDCD, the remainder being solvent or a mixture of solvents with the aminestabilizer. In one embodiment the composition comprises, by weight ofcomposition, greater than 70 wt % of a nitrification inhibitor such asDCD, the remainder being solvent or a mixture of solvents with the aminestabilizer. In one embodiment the composition comprises, by weight ofcomposition, greater than 75 wt % of a nitrification inhibitor such asDCD, the remainder being solvent or a mixture of solvents with the aminestabilizer.

In one embodiment the composition comprises, by weight of composition,greater than 30 wt % of DCD and/or NBPT, the remainder being solvent ora mixture of solvents with the amine stabilizer and dye. By way ofexample, in one embodiment, the fertilizer composition comprises, byweight of composition, 20-30 wt % of NBPT and 70-80 wt % of a solventblend of: (i) at least one dioxolane compound of formula (II.b):

wherein R₆ and R₇ individually comprises a hydrogen, an alkyl group, analkenyl group, or a phenyl group, wherein n is an integer of from 1 to10.

In one embodiment the composition comprises, by weight of composition,greater than 40 pbw of NBPT (or NBPT in combination with DCD), theremainder being solvent or a mixture of solvents.

In one embodiment the composition comprises, by weight of composition,greater than 50 pbw of NBPT (or NBPT in combination with DCD), theremainder being solvent or a mixture of solvents.

Experiments:

Experiment 1—2-Amino-2-methyl-1-propanol: Compositions were prepared bymixing components in the amounts indicated in Table 1. The aminestabilizer utilized was 2-Amino-2-methyl-1-propanol. Composition 1 wasutilized as a comparative example, i.e., without added amine stabilizer.

TABLE 1 Various Compositions with/without 2-Amino-2-methyl-1-propanolComposition Composition Composition 1 2 3 Component wt % wt % wt % NBPT52 52 52 DMSO 48 44 38 2-Amino-2-methyl-1-propanol 0 4 10 Total 100 100100

TABLE 2 Flash point of Compositions (2-Amino-2-methyl-1-propanol) NBPT +DMSO with Initial flash Flash point after 2 2-Amino-2-methyl- pointweeks at 54° C. 1-propanol (wt %) (° C.) (° C.) 0  96.5 52.0  4% 92.190.3 10% 89.3 89.2

Referring to Table 2, the flash point was measured for Composition 1(control), Composition 2 and Composition 3 initially and 2 weeksthereafter. Without an amine stabilizer, the flash point of the NBPTcomposition (i.e., Composition 1) exhibited a dramatic drop from 96.5°C. to 52.0 after 2 weeks at 54° C. The solution was observed to undergoa color change from colorless, initially, to dark brown with anoticeable amount of sediments after 2 weeks at 54° C. The flash pointof NBPT composition with 4% 2-Amino-2-methyl-1-propanol (Composition 2)is stable at around 90° C. after two weeks at 54° C. The sedimentationwas observed to be dramatically reduced as compared to the control. Theflash point of the NBPT composition with 10% 2-Amino-2-methyl-1-propanol(Composition 3) is stable at around 89.2° C. after two weeks at 54° C.Upon observation, only a slight change in the color of the solution andalmost no sedimentation was observed.

Experiment 2—Amino-2-propanol: Compositions were prepared by mixingcomponents in the amounts indicated in Table 3. The amine stabilizerutilized was Amino-2-propanol. Composition 1a was utilized as acomparative example, i.e., without added amine stabilizer.

TABLE 3 Various Compositions with/without Amino-2-propanol Composition1a Composition 2a Composition 3a Component wt % wt % wt % NBPT 52 52 52DMSO 48 44 38 Amino-2-propanol 0 4 10 Total 100 100 100

TABLE 4 Flash point of Compositions with Amino-2-propanol NBPT + DMSOwith Initial flash Flash point after 2 Amino-2-propanol point weeks at54° C. (wt %) (° C.) (° C.) 0  96.5 52.0  4% 92.2 69.6 10% 88.2 75.0

Referring to Table 4, the flash point was measured for Composition 1a(control), Composition 2a and Composition 3a initially and 2 weeksthereafter. Without an amine stabilizer, the flash point of the NBPTcomposition (i.e., Composition 1a) exhibited a dramatic drop from 96.5°C. to 52.0 after 2 weeks at 54° C. The drop in the flash point of theNBPT composition decreases significantly by adding 10% Amino-2-propanol(Composition 3a). It was observed that the addition of the aminestabilizer, Amino-2-propanol, in Compositions 2a and 3a also reducessediments in the solution versus the control.

Experiment 3—2-Amino-1-butanol: Compositions were prepared by mixingcomponents in the amounts indicated in Table 5. The amine stabilizerutilized was 2-Amino-1-butanol. Composition 1b was utilized as acomparative example, i.e., without this added amine stabilizer.

TABLE 5 Composition with/without 2-Amino-1-butanol Composition 1bComposition 2b Composition 3b Component wt % wt % wt % NBPT 52 52 52DMSO 48 44 38 2-Amino-1-butanol 0 4 10 Total 100 100 100

TABLE 6 Flash point of Compositions with 2-Amino-1-butanol NBPT + DMSOwith Initial flash Flash point after 2 2-Amino-1-butanol point weeks at54° C. (wt %) (° C.) (° C.) 0  96.5 52.0  4% 94.1 91.5 10% 93.2 92.6

Referring to Table 6, the flash point was measured for Composition 1 b(control), Composition 2b and Composition 3b initially and 2 weeksthereafter. Without the 2-Amino-1-butanol amine stabilizer, the flashpoint of the control (Composition 1b) exhibited a dramatic drop from96.5° C. to 52.0 after 2 weeks at 54° C. The solution was observed toundergo a color change from colorless to dark brown and produces largeamounts of sediments after 2 weeks at 54° C. The flash point of the NBPTcomposition with 4% 2-Amino-1-butanol (Composition 2b) is stable at91.5° C. after two weeks at 54° C. Sedimentation was observed to bedramatically reduced versus the control. The flash point of NBPTcomposition with 10% 2-Amino-1-butanol (Composition 3b) is stable at92.6° C. after two weeks at 54° C. Only a slight change in the color ofthe solution and almost no sedimentation was observed in solution.

Experiment 4—Amine stabilizer for NBPT+DCD(2-Amino-2-methyl-1-propanol).

TABLE 7 Composition of NBPT + DCD with 2-Amino-2-methyl-1-propanolComposition 1c Composition 2c Component wt % wt % NBPT 6 6 DCD 24 24DMSO 70 68 2-Amino-2-methyl-1-propanol 0 2 Total 100 100

Summary of Observations:

The color of solution of the NBPT and DCD composition (Composition 1c)changes from colorless to amber after 2 weeks at 54° C. The color ofsolution of the NBPT and DCD composition does not change with theaddition of 2% 2-Amino-2-methyl-1-propanol (Composition 2c) after 2weeks at 54° C. This would appear to indicate that Composition 2c ismore stable (degradation stability) over the same period of time versusthe control.

Experiment 5—Amine stabilizer for NBPT+DCD—Amino-2-propanol

TABLE 8 Composition of NBPT + DCD with Amino-2-propanol Composition 1dComposition 2d Component wt % wt % NBPT 6 6 DCD 24 24 DMSO 70 68Amino-2-propanol 0 2 Total 100 100

Summary of Observations:

The color of solution of the NBPT and DCD composition (Composition 1d)changes from colorless to amber after 2 weeks at 54° C. The color ofsolution of the NBPT and DCD composition does not change with theaddition of 2% Amino-2-propanol (Composition 2d) after 2 weeks at 54° C.This would appear to indicate that Composition 2d is more stable(degradation stability) over the same period of time versus the control.

Experiment 6—Amine stabilizer for NBPT+DCD—2-Amino-1-butanol

TABLE 9 Composition of N-Dual with 2-Amino-1-butanol Composition 1eComposition 2e Component wt % wt % NBPT 6 6 DCD 24 24 DMSO 70 682-Amino-1-butanol 0 2 Total 100 100

Summary of Observations:

The color of solution of the NBPT and DCD (Composition 1e) compositionchanges from colorless to amber after 2 weeks at 54° C. The color ofsolution of the NBPT and DCD composition does not change too much withthe addition of 2% 2-Amino-1-butanol (Composition 2e) after 2 weeks at54° C.

What is claimed is:
 1. A stable liquid agricultural compositioncomprising N-(n-butyl)-thiophosphoric triamide (NBPT) urease inhibitor,wherein between 40 and 55 wt. % of the composition isN-(n-butyl)-thiophosphoric triamide (NBPT); dimethyl sulfoxide; and anamine stabilizer selected from the group consisting of aminopropanol,2-amino-1-butanol, and mixtures thereof, wherein the amine stabilizer ispresent in an amount of from 4 wt % to about 15 wt %, by total weight ofthe composition, and wherein there is an absence of each and everycompound according to formula (I.a):

wherein R₁, R₂ and R₃, are each independently chosen from H, a C₁-C₁₆alkyl group, a C₁-C₁₆ alkenyl, group, a C₁-C₁₆ alkoxyalkyl group, aC₇-C₃₀ alkylarylalkyl group, a C₇-C₃₀ arylalkyl group, or an aryl group,provided that at least one of R₁, R₂ and R₃ is not H.
 2. The liquidagricultural composition of claim 1, wherein at least 38 wt. % of thecomposition is DMSO.
 3. The liquid agricultural composition of claim 2,wherein 38 to 44 wt. % of the composition is dimethyl sulfoxide.
 4. Theliquid agricultural composition of claim 1, further comprising at leastone nitrification inhibitor.
 5. The liquid agricultural composition ofclaim 1, wherein between 40 and 50 wt % of the composition is NBPT. 6.The liquid agricultural composition of claim 1, further comprising anodor masking agent comprising at least one of terpineol, 4-allylanisole,limonene, 4-(2,6,6-Trimethyl-2-cyclohexenyl)-3-buten-2-one, isoamylbutyrate, benzaldehyde, diethyl malonate, cyclohexyl acetate, mint, oilJapanese cherry, or α-Ionone.
 7. The liquid agricultural composition ofclaim 1, wherein the N-(n-butyl)-thiophosphoric triamide (NBPT) ispresent in an amount between 50 and 55 wt %, by total weight ofcomposition, wherein the amine stabilizer is2-amino-2-methyl-1-propanol, 2-amino-1-butanol or mixtures thereof, andwherein 38 to 44 wt. % of the composition is DMSO.
 8. The liquidagricultural composition of claim 1, wherein the amine stabilizer ispresent in an amount of from 4 to 5 wt. % by total weight of the liquidagricultural composition.
 9. The liquid agricultural composition ofclaim 1, wherein the aminopropanol is selected from the group consistingof 2-amino-2-methyl-1-propanol, amino-2-propanol, and mixtures thereof.10. A stable liquid agricultural composition comprising: from 14 to 60wt. % at least one urease inhibitor; dimethyl sulfoxide; an aminestabilizer selected from the group consisting of aminopropanol,2-amino-1-butanol, and mixtures thereof, wherein the amine stabilizer ispresent in an amount of from 1 to 15 wt. %, by total weight of thecomposition; optionally, at least one co-solvent selected from the groupconsisting of: (a) at least one dioxolane compound of formula (II.b):

wherein R₆ and R₇ individually comprises a hydrogen, an alkyl group, analkenyl group, or a phenyl group, wherein n is an integer of from 1 to10; b) at least one compound of formula (III):R₃OOC-A-CONR₄R₅  (III), wherein R₃ comprises a C₁-C₃₆ alkyl group;wherein R₄ and R₅ individually comprise a C₁-C₃₆ alkyl group, wherein R₄and R₅ can optionally together form a ring; and wherein A is a linear ora branched divalent C₂-C₁₂ alkyl group; and c) a glycol or glycolderivative; and an odor masking agent comprising at least one ofterpineol, 4-allylanisole, limonene,4-(2,6,6-Trimethyl-2-cyclohexenyl)-3-buten-2-one, isoamyl butyrate,benzaldehyde, diethyl malonate, cyclohexyl acetate, mint, oil Japanesecherry, or α-Ionone, wherein there is an absence of each and everycompound according to formula (I.a):

wherein R₁, R₂ and R₃, are each independently chosen from H, a C₁-C₁₆alkyl group, a C₁-C₁₆ alkenyl, group, a C₁-C₁₆ alkoxyalkyl group, aC₇-C₃₀ alkylarylalkyl group, a C₇-C₃₀ arylalkyl group, or an aryl group,provided that at least one of R₁, R₂ and R₃ is not H.
 11. The liquidagricultural composition of claim 10, further comprising dicyandiamide(DCD) as a nitrification inhibitor, wherein the composition contains 10to 75% total urease inhibitor and nitrification inhibitor.
 12. Theliquid agricultural composition of claim 10, wherein the aminestabilizer is present in an amount of from 4 wt % to about 15 wt %, byweight of composition.
 13. The liquid agricultural composition of claim10, wherein the at least one urease inhibitor is present in an amountbetween 20 and 55 wt %, by total weight of composition.
 14. The liquidagricultural composition of claim 10, wherein the at least one ureaseinhibitor is present in an amount between 50 and 55 wt %, by totalweight of composition.
 15. The liquid agricultural composition of claim10, wherein the aminopropanol is selected from the group consisting of2-amino-2-methyl-1-propanol, amino-2-propanol, and mixtures thereof. 16.A method of making a solid or concentrated liquid fertilizer compositioncomprising contacting one or more nitrogenous fertilizer compounds witha liquid inhibitor composition of claim 1 that comprises between 45 and55 wt. % N-(n-butyl)-thiophosphoric triamide (NBPT) as urease inhibitor,which is dissolved or dispersed in a liquid medium comprising: dimethylsulfoxide, wherein at least 38 wt. % of the composition is dimethylsulfoxide; and an amine stabilizer selected from the group consisting ofaminopropanol, 2-amino-1-butanol and any combination thereof, whereinthe amine stabilizer is present in an amount of from 4 wt % to 15 wt %,by weight of composition, wherein there is an absence of each and everycompound according to formula (I.a):

wherein R₁, R₂ and R₃, are each independently chosen from H, a C₁-C₁₆alkyl group, a C₁-C₁₆ alkenyl, group, a C₁-C₁₆ alkoxyalkyl group, aC₇-C₃₀ alkylarylalkyl group, a C₇-C₃₀ arylalkyl group, or an aryl group,provided that at least one of R₁, R₂ and R₃ is not H.
 17. The method ofclaim 16, wherein the liquid medium further comprises an odor maskingagent comprising at least one of terpineol, 4-allylanisole, limonene,4-(2,6,6-Trimethyl-2-cyclohexenyl)-3-buten-2-one, isoamyl butyrate,benzaldehyde, diethyl malonate, cyclohexyl acetate, mint, oil Japanesecherry, or α-Ionone.
 18. A stable liquid agricultural compositionconsisting of: between 45 and 55 wt. % N-(n-butyl)-thiophosphorictriamide (NBPT) as a urease inhibitor; dimethyl sulfoxide, wherein atleast 38 wt. % of the composition is dimethyl sulfoxide; an aminestabilizer selected from the group consisting of aminopropanol,2-amino-1-butanol, and mixtures thereof, wherein the amine stabilizer ispresent in an amount of from 4 wt % to 10 wt %, by weight of thecomposition; optionally, at least one nitrification inhibitor;optionally, at least one co-solvent selected from the group consistingof: (a) at least one dioxolane compound of formula (II.b):

wherein R₆ and R₇ individually comprises a hydrogen, an alkyl group, analkenyl group, or a phenyl group, wherein n is an integer of from 1 to10; b) at least one compound of formula (III):R₃OOC-A-CONR₄R₅  (III), wherein R₃ comprises a C₁-C₃₆ alkyl group;wherein R₄ and R₅ individually comprise a C₁-C₃₆ alkyl group, wherein R₄and R₅ can optionally together form a ring; and wherein A is a linear ora branched divalent C₂-C₁₂ alkyl group; and c) a glycol, or glycolderivative, or combinations thereof; and optionally, at least one dye;optionally, an odor masking agent selected from at least one member ofthe group consisting of terpineol, 4-allylanisole, limonene,4-(2,6,6-Trimethyl-2-cyclohexenyl)-3-buten-2-one, isoamyl butyrate,benzaldehyde, diethyl malonate, cyclohexyl acetate, mint, oil Japanesecherry, and α-Ionone.
 19. The liquid agricultural composition of claim18, consisting of the N-(n-butyl)-thiophosphoric triamide (NBPT) as theurease inhibitor; the dimethyl sulfoxide, wherein 38 to 44 wt. % of thecomposition is dimethyl sulfoxide; the amine stabilizer; optionally, theat least one nitrification inhibitor; optionally, the at least one dye.